Total syntheses of (+)-chloropuupehenone and (+)-chloropuupehenol and their analogues and evaluation of their bioactivities

…, I Namatame, H Tomoda, EM Perchellet…

Index: Hua, Duy H.; Huang, Xiaodong; Chen, Yi; Battina, Srinivas K.; Tamura, Masafumi; Noh, Sang K.; Koo, Sung I.; Namatame, Ichiji; Tomoda, Hiroshi; Perchellet, Elisabeth M.; Perchellet, Jean-Pierre Journal of Organic Chemistry, 2004 , vol. 69, # 18 p. 6065 - 6078

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Citation Number: 40

Abstract

Tetracyclic pyrans (+)-chloropuupehenone (1) and (+)-chloropuupehenol (5) and its C8-R- isomer (+)-3 were synthesized via a one-pot condensation of 1-chloro-2-lithio-3, 5, 6-tris (tert- butyldimethylsilyloxy) benzene (8) with (4a S, 8a S)-3, 4, 4a, 5, 6, 7, 8, 8a-octahydro-2, 5, 5, 8a-tetramethylnaphthalene-1-carboxaldehyde (7). The major condensation product,(4a S, 6a R, 12b S)-2 H-9, 10-bis (tert-butyldimethylsilyloxy)-11-chloro-1, 3, 4, 4a, 5, 6, 6a, 12b- ...